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Isle of Wight

$59+ Cheap flights from Portland, ME (PWM) to Isle of Wight, VA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — RIC
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Isle of Wight are usually found in September or May, booked 65 days in advance, depart on a Monday or Wednesday and return on a Friday

Cheap flight deals from Portland to Isle of Wight

Keep the following information in mind while searching for Portland to Isle of Wight flight deals. Data was last updated July 29, 2025.

Round-trip from

$118
(Breeze Airways)

One-way from

$59
(Breeze Airways)

Popular in

February

Cheapest in

September

Average price

$336
From Portland to Isle of Wight
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One-way flight from Portland to Isle of Wight
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Highest demand for flights based on searches. 15% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Portland to Isle of Wight

Cheapest flights from Portland to Isle of Wight
Explore the most affordable flight options available from Portland to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Breeze Airways deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/34:41 pmPWM - ORF
Nonstop1h 46mBreeze Airways
Sat 9/62:19 pmORF - PWM
Nonstop1h 42mBreeze Airways
Deal found 7/27$118
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/191:35 pmPWM - ORF
1 stop7h 33mDelta
Mon 9/225:55 pmORF - PWM
1 stop6h 16mDelta
Deal found 7/29$237
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/115:30 amPWM - ORF
1 stop6h 10mSouthwest
Sat 11/1510:05 amORF - PWM
2 stops11h 50mSouthwest
Deal found 7/29$264
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/76:00 amPWM - ORF
1 stop3h 48mAmerican Airlines
Thu 10/97:35 pmORF - PWM
1 stop4h 13mAmerican Airlines
Deal found 7/29$272
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/36:14 amPWM - ORF
1 stop8h 26mUnited Airlines
Sat 9/66:00 amORF - PWM
2 stops11h 42mUnited Airlines
Deal found 7/27$312
This Mytrip deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/218:52 pmPWM - ORF
Nonstop1h 44mMultiple Airlines
Sat 8/235:30 amORF - PWM
3 stops30h 14mMultiple Airlines
Deal found 7/27$388

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Isle of Wight that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2025.
Use the filters below to find and compare flights from Portland to Isle of Wight that are best for you.

Fly from

Portland

Fly to

Isle of Wight

Route

Depart

Return

Price

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Wed 9/3

4:41 pm-6:27 pm

Nonstop1h 46m

Norfolk

Sat 9/6

2:19 pm-4:01 pm

Nonstop1h 42m

$118

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Fri 9/19

1:35 pm-9:08 pm

1 stop7h 33m

Norfolk

Mon 9/22

5:55 pm-12:11 am

1 stop6h 16m

$237

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Tue 11/11

5:30 am-11:40 am

1 stop6h 10m

Norfolk

Sat 11/15

10:05 am-9:55 pm

2 stops11h 50m

$264

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Tue 10/7

6:00 am-9:48 am

1 stop3h 48m

Norfolk

Thu 10/9

7:35 pm-11:48 pm

1 stop4h 13m

$272

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Wed 9/3

6:14 am-2:40 pm

1 stop8h 26m

Norfolk

Sat 9/6

6:00 am-5:42 pm

2 stops11h 42m

$312

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Thu 8/21

8:52 pm-10:36 pm

Nonstop1h 44m

Norfolk

Sat 8/23

5:30 am-11:44 am

3 stops30h 14m

$388

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Thu 8/28

8:52 pm-10:36 pm

Nonstop1h 44m

$59

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Wed 8/27

3:53 pm-10:56 pm

1 stop7h 03m

$119

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Wed 8/27

10:30 am-9:40 pm

2 stops11h 10m

$124

PortlandNorfolk

PWM - ORF

PWMORF

Portland

Wed 8/13

6:00 am-10:16 am

1 stop4h 16m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 12 results
1
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Best time to book a flight from Portland to Isle of Wight

Have a flexible travel schedule? Discover the best time to fly to Isle of Wight from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Isle of Wight

How far ahead should I book a flight from Portland, Maine to Isle of Wight?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Isle of Wight. Price data was last updated on July 25, 2025.

The price you pay for your flight from Portland, Maine to Isle of Wight may vary depending on when you book. For the best chance of a lower fare, look to book 30 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Portland, Maine to Isle of Wight?

Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Isle of Wight (average of $281). Flying from Portland, Maine to Isle of Wight in March is currently the most expensive (average of $351). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PWM to I1W?

Find hourly flight availability from Portland to Isle of Wight. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2025.

When flying from Portland, Maine to Isle of Wight, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Portland, Maine to Isle of Wight?

Use this chart to determine the cheapest time to fly round-trip from Portland to Isle of Wight. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland, Maine to Isle of Wight flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Isle of Wight

Get insights into the airlines that provide service to Isle of Wight. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Isle of Wight. Reviews last updated July 29, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Breeze Airways from Portland to Isle of Wight to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
190 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Portland to Isle of Wight. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Isle of Wight?

    For a flight from Portland to Isle of Wight, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 0 outbound flights to Isle of Wight per day. 5 airlines have flights to Isle of Wight from Portland on a regular basis.

  • What are the cheapest airlines to fly from Portland, Maine to Isle of Wight one-way?

    One-way options have recently been found by users for as low as $59 on Breeze Airways. Other airlines that offer cheap prices include American Airlines from $119 and Southwest from $124 one-way.

  • Can I find deals for flights from Portland to Isle of Wight that include hotel bookings?

    Yes. In addition to deals on Portland to Isle of Wight flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Isle of Wight?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Isle of Wight.

  • Can I find deals for business class flights from Portland to Isle of Wight?

    Yes. Cheapflights offers flight deals from Portland to Isle of Wight by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Isle of Wight?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Isle of Wight (average of $281). Flying from Portland, Maine to Isle of Wight in March is currently the most expensive (average of $351). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 5 airlines flying from Portland to Isle of Wight

Discover the top 5 airlines that operate flights from Portland to Isle of Wight. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$67Average$158FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$120Average$305FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$194Average$363FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$218Average$339FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$246Average$382FlexibilityNo cancel feeOn-time69%

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